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Cal Fussman (@calfussman) is a New York Times bestselling author and a writer-at-large for Esquire magazine, where he is best known for being a primary writer of the “What I’ve Learned” feature. He has transformed oral history into an art form, conducting probing interviews with a long list of icons who’ve shaped the last 50 years of world history.

I’ve been trying to get Cal to do his own podcast. Rather than overthinking it, I simply asked Cal to interview a friend who I would also love to have on the podcast: Larry King. This episode is the result of that request.

Larry King (@kingsthings) has been dubbed “The most remarkable talk show host on TV, ever” by TV Guide and “Master of the mic” by Time Magazine. Larry’s been described as the Muhammad Ali of the broadcast interview, and he’s been inducted into five of the nation’s leading broadcasting halls of fame. He’s the recipient of the Allen H. Neuharth Award for Excellence in Journalism, an Emmy, the George Foster Peabody Award for Excellence in Broadcasting, ten CableACE awards — the list goes on.

Want to hear my first episode with Cal Fussman? — In this episode, we discuss Cal’s interviews with the most influential people in history, how he made himself a guinea pig (Cal boxed against world champion Julio Cesar Chavez), and his best life lessons (stream below or right-click here to download):

This podcast is brought to you by Shopify. With the help of Shopify, many readers of my blog — first-time business owners — have ended up making millions of dollars each with their side gigs. Back in 2009, I helped create Shopify’s Build a Business, which is now the world’s largest entrepreneurship competition.

The goal of this competition is to entice would-be entrepreneurs to get off the couch and make things happen, and all you have to do to qualify is open a store on Shopify and start selling. Top sellers in each category then have the exclusive opportunity to learn from mentors and experts like Tony Robbins, Daymond John, Seth Godin, Sir Richard Branson, and me a location like Oheka (aka Gatsby’s) Castle or Necker Island.

Listeners to this show can go to shopify.com/tim to sign up for a free, 30-day trial and get access to video courses that will help you get started — including How to Quickly Start a Profitable Dropshipping Store with Corey Ferreira and some goodies from me. Check it out at shopify.com/tim today!

This podcast is also brought to you by Kettle & Fire, which makes some of the best bone broth I’ve ever tasted. It came highly recommended by past podcast guests such as Amelia Boone and Dr. Dom D’Agostino.

Kettle & Fire is the first shelf-stable (i.e. never frozen) bone broth that uses bones from 100% grass-fed, organically raised animals. They use longer cook times (20+ hours), which means more collagen and other nutrients.Visit Kettleandfire.com/tim and you can receive 20% off your entire order.

QUESTION(S) OF THE DAY: What was your favorite quote or lesson from this episode? Please let me know in the comments.

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Bill Rasmussen (@bill_espn) is the co-founder of ESPN. He turned a massive gamble into an opportunity to create the 24-hour programming cycle used universally by networks today.

This episode comes from my new television show Fear(less), where I interview world-class performers about how they’ve overcome doubt, conquered fear, and made their toughest decisions. You can watch the entire first episode with illusionist David Blaine for free at att.net/fearless. (To watch all episodes, please visit DIRECTV NOW).

We recorded three hours of material and only one hour was used for the TV show. This podcast episode is almost entirely new content that didn’t appear on TV.

Want to hear another podcast with a guest from Fearless? — Listen to this episode with Micahel Gervais. We discuss how to win the war against anxiety, some of the more effective (and less effective) ways to self-talk, behind-the-scenes stories of Michael’s clients, understanding mastery, and much more. (stream below or right-click here to download):

This podcast is brought to you by Ascent Protein, the only US-based company that offers native proteins — both whey and micellar casein — directly to the consumer for improved muscle health and performance.

Because the product is sourced from Ascent’s parent company, Leprino Foods — the largest producer of mozzarella cheese in the world — it’s entirely free of artificial ingredients and completely bypasses the bleaching process common to most other whey products on the market.

This podcast is also brought to you by Four Sigmatic. I reached out to these Finnish entrepreneurs after a very talented acrobat introduced me to one of their products, which blew my mind (in the best way possible). It is mushroom coffee featuring chaga. It tastes like coffee, but there are only 40 milligrams of caffeine, so it has less than half of what you would find in a regular cup of coffee. I do not get any jitters, acid reflux, or any type of stomach burn. It put me on fire for an entire day, and I only had half of the packet.

People are always asking me what I use for cognitive enhancement, and right now this is the answer. You can try it right now by going to foursigmatic.com/tim and using the code Tim to get 20 percent off your first order. If you are in the experimental mindset, I do not think you’ll be disappointed.

QUESTION OF THE DAY: What was your favorite quote or lesson from this episode? Please let me know in the comments.

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In this episode, I answer the most upvoted questions from subscribers to 5-Bullet Friday, the free newsletter I send out every week.

In this Q&A, I answer your most popular questions, including:

Physical training

Interview prep

The art of networking

Education reform

Dream guests on the show

And much more.

Want to ask me your own questions? Just subscribe to 5-Bullet Friday, which — every Friday — sends five bullet points of cool things I’ve found that week, including apps, books, gadgets, albums, articles, new hacks or tricks, and — of course — all sorts of weird stuff I dig up around the world. It’s free, it’s always going to be free, and you can check it out here: tim.blog/friday.

This podcast is brought to you by WordPress, my go-to platform for 24/7-supported, zero downtime blogging, writing online, creating websites — everything! I love it to bits, and the lead developer, Matt Mullenweg, has appeared on this podcast many times.

Whether for personal use or business, you’re in good company with WordPress — used by The New Yorker, Jay Z, FiveThirtyEight, TechCrunch, TED, CNN, and Time, just to name a few. A source at Google told me that WordPress offers “the best out-of-the-box SEO imaginable,” which is probably why it runs nearly 30% of the Internet. Go to WordPress.com/Tim to get 15% off your website today!

This podcast is also brought to you by Four Sigmatic. I reached out to these Finnish entrepreneurs after a very talented acrobat introduced me to one of their products, which blew my mind (in the best way possible). It is mushroom coffee featuring chaga. It tastes like coffee, but there are only 40 milligrams of caffeine, so it has less than half of what you would find in a regular cup of coffee. I do not get any jitters, acid reflux, or any type of stomach burn. It put me on fire for an entire day, and I only had half of the packet.

People are always asking me what I use for cognitive enhancement, and right now this is the answer. You can try it right now by going to foursigmatic.com/tim and using the code Tim to get 20 percent off your first order. If you are in the experimental mindset, I do not think you’ll be disappointed.

QUESTION(S) OF THE DAY: What was your favorite quote or lesson from this episode? Please let me know in the comments.

In particular, this post focuses on questions to ask founders before you invest, but it also serves as a tutorial on how to ask better questions in life and in business.

Enter Jason

A THOUSAND FIRST DATES

The life of an angel is all about managing a deal funnel, which includes three distinct steps: sourcing deals, evaluating deals, and, finally, picking which founders you’re going to fund.

Meeting with founders for an hour is the most frequent technique for angels to decide who to invest in, but certainly not the only one. There are some angels whose primary technique for selecting investments is to follow other smart investors, drafting off of their meetings and deal flow.

Another technique is simply to review the core metrics and decide based on those. This can be done by reviewing a deck or by checking public information sources, like the App Store rankings, and traffic monitoring services, like Alexa and Quantcast.

Some investors have a huge Rolodex and simply invest in the founders they already know, a technique that worked extremely well for investors who knew Elon Musk (Zip2 and PayPal before Tesla and SpaceX), Evan Williams (Blogger before Twitter), and Mark Pincus (Freeloader and Tribe before Zynga).

Of course, the “invest in who you know” approach would mean you missed the biggest startups in history: Mark Zuckerberg, Bill Gates, Evan Spiegel, and Larry Page, who all hit the ball out of the park on their first try—at the ages of nineteen, twenty, twenty-one, and twenty-five, respectively.

Meetings are important and free. You should take a lot of them. Ten one-hour meetings a week is a good target for a professional angel. Half that if you’re doing this part-time.

My best advice to you as you start dating is to be promiscuous with meetings—but a prude when it comes to writing checks. Don’t be a tramp like I was.

I’m going to take you through the four most important questions I ask all founders. The goal of asking these questions is not just for you to understand the business but also so you yourself can answer four critical investor questions:

Why has this founder chosen this business?

How committed is this founder?

What are this founder’s chances of succeeding in this business—and in life?

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Michael Gervais (@michaelgervais) is the performance psychologist elite athletes and coaches turn to when they want to level up or when they’re returning from hard times and want to not just get back to where they were, but exceed their previous highest levels of excellence. His clients include Olympic gold medalists, Super Bowl champion NFL coaches, you name it.

In this episode, we discuss how to win the war against anxiety, some of the more effective (and less effective) ways to self-talk, behind-the-scenes stories of Michael’s clients, understanding mastery, and much more.

This episode comes from my new television show Fear{less}, where I interview world-class performers on stage about how they’ve overcome doubt, conquered fear, and made their toughest decisions. You can watch the entire first episode with illusionist David Blaine for free at att.net/fearless. (To watch all episodes, please visit DIRECTV NOW.)

We recorded three hours of material and only one hour was used for the TV show. This podcast episode is almost entirely new content that didn’t appear on TV.

This podcast is brought to you by Ascent Protein, the only US-based company that offers native proteins — both whey and micellar casein — directly to the consumer for improved muscle health and performance. Because the product is sourced from Ascent’s parent company, Leprino Foods — the largest producer of mozzarella cheese in the world — it’s entirely free of artificial ingredients and completely bypasses the bleaching process common to most other whey products on the market.

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“You will fall. And when you fall, the winner always gets up, and the loser stays down.”
-Arnold Schwarzenegger

In this episode, we discuss another frequently requested question from listeners. I’ve gathered some of the best advice about coping with frustrations and roadblocks, and — ultimately — learning how to turn failure into success.

These conversations are extremely valuable because they show you there is more than one way to achieve your goals. After more than 200 conversations with the world’s top performers, you start to spot certain patterns. These are the shared habits, hacks, philosophies, and tools that are the common threads of success, happiness, health, and wealth. Behind each success story is usually a lesson on how to overcome failure. Aside from my own take on the topic, this episode includes conversations with:

This podcast is brought to you by Soothe.com, the world’s largest on-demand massage service. Because I’ve been broken so many times, I have body work done at least twice a week — so I have a high bar for this stuff. I do not accept mediocrity, and I wouldn’t expect you to, either.

After much personal testing, I can affirm that Soothe delivers a hand-selected, licensed, and experienced massage therapist to you in the comfort of your own home, hotel, or office in as little as an hour. I was amazed at the quality of service and convenience. Think of it as Uber for massages, available in fifty cities worldwide. Download the app at Soothe.com and use code TIM to get $20 off each of your first two massages.

This podcast is also brought to you by MeUndies. I’ve spent the last year wearing underwear from these guys 24/7, and they are the most comfortable and colorful underwear I’ve ever owned. MeUndies are designed in L.A. and made from sustainably sourced MicroModal — a fabric three times softer than cotton. Even better, it includes free shipping.

If you don’t love your first pair of MeUndies, they’ll hook you up with a new pair or a refund. If you love the product, they have three different subscription plans — so you’ll never be bored with the ever-changing selection. Check out MeUndies.com/Tim to see my current faves (some are awesomely ridiculous, like the camo) and get 20 percent off your first pair. That’s MeUndies.com/Tim.

QUESTION(S) OF THE DAY: What was your favorite quote or lesson from this episode? Please let me know in the comments.

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“Remember: it’s not a failure until you accept defeat.” -Debbie Millman

I’m very excited to share this episode. It’s our first “roundtable” approach to discussing a single topic. This came about when I asked 5-Bullet Friday subscribers (sign up here if you’re interested) to send me questions, and one that stuck out was: Where’s the line between stubbornly pursuing an idea that isn’t working and the patience and persistence needed to actually make it work? In other words — when should you give up and quit and when should you push on?

Since this is something I myself have struggled with, I came to the conclusion that I should reach out to people who might have a better answer. So, I sent the question to the following entrepreneurs, authors, and innovators:

Want to hear my first episode with Debbie Millman?— Listen to this episode, where we discuss how to recover from rejection, how to overcome personal crises of faith, class exercises from her most impactful mentors, and much more. (stream below or right-click here to download):

This podcast is brought to you by Shopify. With the help of Shopify, many readers of my blog — first-time business owners — have ended up making millions of dollars each with their side gigs. Back in 2009, I helped create Shopify’s Build a Business, which is now the world’s largest entrepreneurship competition.

The goal of this competition is to entice would-be entrepreneurs to get off the couch and make things happen, and all you have to do to qualify is open a store on Shopify and start selling. Top sellers in each category then have the exclusive opportunity to learn from mentors and experts like Tony Robbins, Daymond John, Seth Godin, Sir Richard Branson, and me in a location like Necker Island.

Listeners to this show can go to shopify.com/tim to sign up for a free, 30-day trial and gain access to video courses that will help you get started — including “How to Quickly Start a Profitable Dropshipping Store” with Corey Ferreira and some goodies from me. Check it out at shopify.com/tim today!

This podcast is also brought to you by 99Designs,the world’s largest marketplace of graphic designers. I have used them for years to create some amazing designs. When your business needs a logo, website design, business card, or anything you can imagine, check out 99Designs.

I used them to rapid prototype the cover for The Tao of Seneca, and I’ve also had them help with display advertising and illustrations. If you want a more personalized approach, I recommend their 1-on-1 service. You get original designs from designers around the world. The best part? You provide your feedback, and then you end up with a product that you’re happy with or your money back. Click this link and get a free $99 upgrade. Give it a test run…

QUESTION(S) OF THE DAY: What was your favorite quote or lesson from this episode? Please let me know in the comments.